Cellulose organic ester composition containing phenylethyl benzoate



Patented Feb: 28, 193 i a cal-Ti n HENRY B. sirrrrnor ROCHESTER,NEWYORK;fASSiGINOR1E01!;AS'11IUMH xonaxconrm,

orinocnasrnn; NEWTYORK; A CORPOR-ATIONYOF'V NEW YORK a I ,GELLU'LOSE oRGANIc-EsTERIcoMPosITioN coN'rAmmG rnnmn'rm mumm- 5 v No Drawing? This invention relates to compositionsgof f matter in which cellulose organic esters, such as cellulose acetate, are eombinedor mixed with other substances, such as a compatible-v 5 plasticizer, with "or without 'a common solvent for both, and with or Without other useful addition agents, so thatthe result ing product will have properties such as will make the composition highly advantageous forns'e in the'pla'stic and analogous arts,

such, or instance, as the manufacture of Wrapping sheetsor tissues, photographic film; artificial silk, molding compounds or prod v, uets, varnishes or lacquers and the like."

into permanently transparentystron and -flexib1e sheets 'orfilms of desired thinness which are substantially waterproof,-areun-- aflectediby ordinaryphotographi'c fluids and possess the desired properties of a support for sensitive photographic coatings.- An-' other object-of myxmvention is to produce compositions which are capable of easy and convenient manipulation in the plastic and analogous arts,such' as in themanufacture ofsheets, films, artificial silkfilaments,varnishe's, lacquers and the like, and to produce compositions which will not injure, or injured by, the'substances" or surfaces with which I they are associated during; manufactare; Another object of'my-inv'entio'n' is to produce compositions-which can be molded I I atelevated temperatures and high pressures;

to produce plastic products havin the de-; ther 'ob-. jects will'becomeapparent to those-skilled in the art to which-this invention pertains, p While cellulose acetate has beenkriown sirable roperties of; celluloid. f

for' deeadesit has alsofbeen known that to utilize it in various plastieart's it is necessary to mix therewith 'such -rplasticizing or conditioning agents as triphenyl phosphate,

monochlornaphthalene or the like; Certain ofthese'and other addition agents are also added for the purpose of reducing the ;cin-c flammability of the product. Plastic inducing agents, such as the, higher alcohols and theiresters, are sometimes alsoadded." Sim-' ilarly, addition compounds of various kinds One object of this invention is to produce] compositions of matter which may ibe made ,tions'containing arehereina'fter enumer- Application filed February 10,f1932.' seam. 592,132.

have been employed to increase flexibility,

. transparency, toughness and other properties; i which will enhance the valueof the result-Z ing' product. Addition' products for the same or similarpurposes are also added to cellulose; acetate to prepareit for use in the other-plastic'arts,such as in the manufacture of lacquers, varnishes, artificial silk filaments', molded compounds and the; like. While the plasticizers or other addition agents heretofore discovered have had their utility in the art, the increasing, use to which i cellulose acetate has been put and the increasc 1 ingnumber of desirable properties required of celluloseacetate for most purposes have made the discovery 1 of new and economical plasticizersor other'addition agents a matter of considerable importance to the art. This has been aproblemof some difiiculty, since many of'the nitroeellulosesolvents arenot solvents for cellulose acetate," and many. sub stances which act: as plasticizers for nitrocel- I lulose arenot suflieiently compatible w'ithcel-' lulose acetate tobe used asplasticizers infcellulose acetate'compositions. q '7 I havediseovered hat valuable properties maybe induced in and/or. contributed to compositions "containing cellulose organic esters, such as eellulose acetate, by adding thereto as a plasticizing compound phenylethyli benzoate. the-formula: 1

'It is; compatible witheellulose organic esters in "the percentages hereinafter given: The

particularlyusefu1 properties which it in duces in or contributes tocellulosic composiated; g '1 i "Phenylethyl, benzoate may be prepared pin thefollowing manner." A'mixture of 340 of phenylethyl a1oh01, 450 gli of benzoic acid and 15 cc. of concentrated sulfuric acid" is warmedon thesteam bath: Water 'soon' begins toseparate; Heating, on the steam bath is 1 continued overnight; The productis the'ndissolved in 'etherand freed of excess benzoic acid byshaking with dilute sodium hydroxide and finally with water. The ether Phenylethyl benzoatehas is distilled OE, and the residue is distilled under reduced pressure. The fraction coming over at 204 to 206 C. at 25 mm. pressure is collected.

5 In order that those skilled in this art may better understand my invention 1- would state, byway of illustration, that for the manufacture of photographic film or other sheets my new composition of matter may be-compoundedas follows: 100 parts of;-

acetone-soluble cellulose acetate, that is, cellulose. acetate containingfrom 3.6% to 42% acetyl radical, approximately, is dissolved with stirring at atmospheric temperature in 300 to 500 parts, preferably 400 parts, by

whether it is desired to have a more or less freely flowing composition, respectively.

"A composition of matter prepared as above. described may be deposited upon any suit-' able film-forming surface to form a film or sheet, in a manner well known to those skilled in the art. A film so produced has permanently brilliant transparency (even where as much as 50 parts of the plasticizer per 100 parts of cellulose organic ester, such .as cellulose acetate,is used) and low inflammability, burning no morereadily than ordinary newsprint. A film containing 50 parts of phenylethyl benzoate per 100 parts of cellu- 405 lose acetate has the unexpected property ofv superior flatnessaproperty which is much sought form the art but seldom discovered. Films or sheets produced inaccordance with my' invention. are quite tough and flexible. For instance, a film of celluloseacetate 'plas' ticized with %:(parts by weight basedon the cellulose acetate) of phenylethyl benzoate had an initial flexibility of-65% higher than film containing no plasticizer. Furthermore, film s0 plasticized' maintains fiexis bility in a superiorfashion. For instance,"

film containing 50% of phenylethyl benzoate maintained'fiexibility at 65 0., for360 days, Whereasan unplasticized film became brittle in 30 days, all of which indicates that films so plasticized will withstand ordinary usage satisfactorily for many years.

'Other similar solvents (instead of acetone) which 'are compatible with" cellulose acetate and my new plast'icizer may also occur to' those skilled in this art. In like manner this plasticizer may be compounded with other single organicesters of cellulose, such as eel lulose propionate, biity rate and the like, or

with mixed organicjesters, such as cellulose aceto-stearate, cellulose aceto-propionate, or cellulose aceto-malate, a suitable solvent which will dissolve both the cellulose ester and the plasticizer being employed.

Inasmuch as my above-described compositions of matter are useful in the production of films and sheets, it will be apparent that my new plasticizer may also be employed with advanta e in the other branches of the plastic art. for instance, my above-described compositions of matter may be employed in the manufacture of artificial silk by the dry spinning method. With the proper coagulating hath .theymay also be employed for wet spinning. It may be desired to employ compositions of different viscosity or evaporation characteristics, but this is a mere matter of changing the solvent proportion or adding evaporation retardents or other high ormedium-hoiling constituents, as has been well known in the art for more than a decade. My novel plastic-izer may also be employed with advantagev in connection with a number of the known lacquer and varnish formulae with which it may be found to be compatible. In such cases the plasticizer is usually first put into solution with the cellulose ester solution, and if non-solvents are added for the purpose of cheapening the composition, they are added only to such an extent as will not precipitate the cellulose ester from solution. 7 Also the plasticizer is usually employed in comparatively large amounts, such as from 50 to 60 parts, in compoundingllacquersu .Other uses within the scope ofmy invention will also suggest themselves to those skilled in the art and are to be included within the scope of the claims appended hereto. 1

Phenylethyl benzoate may also be advantageously used as a plasticizer in cellulose acetate molding compositions. For instance, when from 20% to 30% (parts by weight based on the cellulose acetate) of phenylethyl benzoate isohomogeneously mixed with cellulose acetate, this mixture may be converted into a hard, translucent plastic prodnot by molding at atemperature of from 140 C. to 160 C; and a pressure of from 2500 pounds to .4000 pounds per square inch for a period of from 1 to 3 minutes, approximately, in a manner already known to those skilled in molding compounds of that nature.

What I claim as my invention and desire to be secured by: Letters Patent of the United States is:

1. A composition ofmatter comprising a cellulose organic ester and phenylethyl benzoate.

2. A composition of matter comprising cellulose'aoetate and phenylethyl benzoate.

3. .A composition of matter comprising 100 parts of cellulose acetate and from 5 to 55 parts, by weight, of phenylethyl benzoate.

4. A relatively thin sheet having the prop- 0 January 1932.

erty of maintaining its original flatness and comprising a cellulose-organic ester and phenylethyl benzoate.

5. A relatively thin sheet havin the property of maintaining its original atness and comprising 100 parts of cellulose acetate and approximately 30 to 50-parts, by weight, of

phenyl'ethyl benzoate. n

6. A molding composition; adapted to molding under elevated temperatures and high pressures, comprising; cellulose acetate and phenylethyl benzoate.

7. A moldlng composltion adapted to molding under elevated temperatures and: high pressures, c0mprising'100 parts of eellulose acetate and approximately to 30 parts, by weight, of phenylethyl benzoate.

Signed at Rochester, N. Y., this Gthday of HENRY B. SMITH. 

